Trichloroisocyanuric Acid → HCID 86601041, compound

HRID 1994372Notes

Reaction equation

HRID 1994372 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C@H:16]([C:17](=[O:30])[NH:18][C@H:19]([CH2:28][OH:29])[CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@@H:15]2[CH2:31][C@H:12]1[CH2:13][CH2:14]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[C@H:16]([C:17](=[O:30])[NH:18][C@H:19]([CH:28]=[O:29])[CH2:20][C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])[C@@H:15]2[CH2:31][C@H:12]1[CH2:13][CH2:14]2)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6909Trichloroisocyanuric AcidHCID 66868028HCID 66868028, compound

Product 1

HCID 86601041HCID 86601041, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (1R,3S,4S)-3((S)-2-tert-Butoxycarbonyl-1-hydroxymethyl-ethylcarbamoyl)-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid benzyl ester (1.1 g) in DCM (10 ml) was cooled to 0° C. under nitrogen. 2,2,6,6-tetramethylpiperidinyloxy (TEMPO, 4 mg) was then added followed by trichloroisocyanuric acid (621 mg) portionwise over 30 minutes. The mixture was stirred at ambient temperature for 1 hour, then filtered through celite. The filtrate was washed with water, 1M sodium thiosulfate solution and brine. Drying over magnesium sulfate and concentration under reduced pressure gave the sub-title compound as a colorless oil (698 mg, 64%); 1H NMR (400 MHz, d-6 DMSO) δ 1.16-1.89 (16H, m), 2.30-2.80 (2H, m), 3.68-3.81 (1H, m), 4.19 (1H, brm), 4.39 (1H, m), 4.91-5.16 (2H, m), 7.21-7.43 (5H, m), 8.45 (0.4H, d), 8.60 (0.6, d), 9.19 (0.6H, S), 9.37 (0.4H, s).

Workup

  1. addition2,2,6,6-tetramethylpiperidinyloxy (TEMPO, 4 mg) was then added
  2. filtrationfiltered through celite
  3. washThe filtrate was washed with water, 1M sodium thiosulfate solution and brine
  4. dry with materialDrying over magnesium sulfate and concentration under reduced pressure

Sources & evidence

ORD record
ord-93686c5023554f11b3350c1426731964
Source dataset
uspto-grants-2010_01
Patent number
US07652153B2

Reaction notes

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